Yesterday and today I played around with it on Gentoo Linux. I was able to replace my system's OpenSSL completely with LibreSSL and with few exceptions was able to successfully rebuild all packages using OpenSSL.

After getting this running on my own system I installed it on a test server. The Webpage tlsfun.de runs on that server. The functionality changes are limited, the only thing visible from the outside is the support for the experimental, not yet standardized ChaCha20-Poly1305 cipher suites, which is a nice thing.

A warning ahead: This is experimental, in no way stable or supported and if you try any of this you do it at your own risk. Please report any bugs you have with my overlay to me or leave a comment and don't disturb anyone else (from Gentoo or LibreSSL) with it. If you want to try it, you can get a portage overlay in a subversion repository. You can check it out with this command:svn co https://svn.hboeck.de/libressl-overlay/git clone https://github.com/gentoo/libressl.git

This is what I had to do to get things running:

LibreSSL itself

First of all the Gentoo tree contains a lot of packages that directly depend on openssl, so I couldn't just replace that. The correct solution to handle such issues would be to create a virtual package and change all packages depending directly on openssl to depend on the virtual. This is already discussed in the appropriate Gentoo bug, but this would mean patching hundreds of packages so I skipped it and worked around it by leaving a fake openssl package in place that itself depends on libressl.

LibreSSL deprecates some APIs from OpenSSL. The first thing that stopped me was that various programs use the functions RAND_egd() and RAND_egd_bytes(). I didn't know until yesterday what egd is. It stands for Entropy Gathering Daemon and is a tool written in perl meant to replace the functionality of /dev/(u)random on non-Linux-systems. The LibreSSL-developers consider it insecure and after having read what it is I have to agree. However, the removal of those functions causes many packages not to build, upon them wget, python and ruby. My workaround was to add two dummy functions that just return -1, which is the error code if the Entropy Gathering Daemon is not available. So the API still behaves like expected. I also posted the patch upstream, but the LibreSSL devs don't like it. So on the long term it's probably better to fix applications to stop trying to use egd, but for now these dummy functions make it easier for me to build my system.

The second issue popping up was that the libcrypto.so from libressl contains an undefined main() function symbol which causes linking problems with a couple of applications (subversion, xorg-server, hexchat). According to upstream this undefined symbol is intended and most likely these are bugs in the applications having linking problems. However, for now it was easier for me to patch the symbol out instead of fixing all the apps. Like the egd issue on the long term fixing the applications is better.

The third issue was that LibreSSL doesn't ship pkg-config (.pc) files, some apps use them to get the correct compilation flags. I grabbed the ones from openssl and adjusted them accordingly.

OpenSSH

This was the most interesting issue from all of them.

To understand this you have to understand how both LibreSSL and OpenSSH are developed. They are both from OpenBSD and they use some functions that are only available there. To allow them to be built on other systems they release portable versions which ship the missing OpenBSD-only-functions. One of them is arc4random().

Both LibreSSL and OpenSSH ship their compatibility version of arc4random(). The one from OpenSSH calls RAND_bytes(), which is a function from OpenSSL. The RAND_bytes() function from LibreSSL however calls arc4random(). Due to the linking order OpenSSH uses its own arc4random(). So what we have here is a nice recursion. arc4random() and RAND_bytes() try to call each other. The result is a segfault.

I fixed it by using the LibreSSL arc4random.c file for OpenSSH. I had to copy another function called arc4random_stir() from OpenSSH's arc4random.c and the header file thread_private.h. Surprisingly, this seems to work flawlessly.

Net-SSLeay

This package contains the perl bindings for openssl. The problem is a check for the openssl version string that expected the name OpenSSL and a version number with three numbers and a letter (like 1.0.1h). LibreSSL prints the version 2.0. I just hardcoded the OpenSSL version numer, which is not a real fix, but it works for now.

SpamAssassin

SpamAssassin's code for spamc requires SSLv2 functions to be available. SSLv2 is heavily insecure and should not be used at all and therefore the LibreSSL devs have removed all SSLv2 function calls. Luckily, Debian had a patch to remove SSLv2 that I could use.

libesmtp / gwenhywfar

Some DES-related functions (DES is the old Data Encryption Standard) in OpenSSL are available in two forms: With uppercase DES_ and with lowercase des_. I can only guess that the des_ variants are for backwards compatibliity with some very old versions of OpenSSL. According to the docs the DES_ variants should be used. LibreSSL has removed the des_ variants.

For gwenhywfar I wrote a small patch and sent it upstream. For libesmtp all the code was in ntlm. After reading that ntlm is an ancient, proprietary Microsoft authentication protocol I decided that I don't need that anyway so I just added --disable-ntlm to the ebuild.

Dovecot

In Dovecot two issues popped up. LibreSSL removed the SSL Compression functionality (which is good, because since the CRIME attack we know it's not secure). Dovecot's configure script checks for it, but the check doesn't work. It checks for a function that LibreSSL keeps as a stub. For now I just disabled the check in the configure script. The solution is probably to remove all remaining stub functions. The configure script could probably also be changed to work in any case.

The second issue was that the Dovecot code has some #ifdef clauses that check the openssl version number for the ECDH auto functionality that has been added in OpenSSL 1.0.2 beta versions. As the LibreSSL version number 2.0 is higher than 1.0.2 it thinks it is newer and tries to enable it, but the code is not present in LibreSSL. I changed the #ifdefs to check for the actual functionality by checking a constant defined by the ECDH auto code.

Apache httpd

The Apache http compilation complained about a missing ENGINE_CTRL_CHIL_SET_FORKCHECK. I have no idea what it does, but I found a patch to fix the issue, so I didn't investigate it further.

> Yesterday and today I played around with it on Gentoo Linux. I was able to replace my system's OpenSSL completely with LibreSSL and with few exceptions was able to successfully rebuild all packages using OpenSSL.

> For libesmtp all the code was in ntlm. After reading that ntlm is an ancient, proprietary Microsoft authentication protocol I decided that I don't need that anyway so I just added --disable-ntlm to the ebuild.

NTLM might be old and, even though Microsoft discourages doing so, it is still being used even in their own products, i.e. it's the only way to authenticate to their Exchange server using SMTP on unix-like systems (i.e. if your company uses Exchange and you use mutt, Thundebird, etc - you are stuck using the web interface) or even between the Exchange server and Outlook when the client is not, or outside, of the AD domain.